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Vitamin K3
Cas No: 58-27-5
No Data 1000 Gram 1 Metric Ton/Day HENAN JIXIANG CO.,LTD Contact Supplier
Menadione Manufacturer/High quality/Best price/In stock
Cas No: 58-27-5
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality 2-Methyl-1,4-naphthoquinone with best price cas:58-27-5
Cas No: 58-27-5
USD $ 110.0-160.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
High quality Vitamin K3 supplier in China
Cas No: 58-27-5
No Data 25 Kilogram 60 Metric Ton/Year Simagchem Corporation Contact Supplier
Menadione CAS:58-27-5 Safe delivery Free of customs clearance
Cas No: 58-27-5
USD $ 1.0-10.0 / Kilogram 1 Kilogram 5000 Kilogram/Month WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
Sodium ascorbate, food additive and USP grade
Cas No: 58-27-5
USD $ 1.0-1.0 / Kilogram 1 Kilogram 10 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier
99% vitamin K / vitamin K3
Cas No: 58-27-5
USD $ 40.0-50.0 / Kilogram 2 Kilogram Metric Ton/Day Xi'an Harmonious Natural Bio-Technology Co., Ltd. Contact Supplier
Top quality CAS 58-27-5 / Vitamine K3 / Menadione
Cas No: 58-27-5
No Data 25 Kilogram 25 Metric Ton/Month Hefei TNJ chemical industry co.,ltd Contact Supplier
High quality Chinese supplier Vitamin K3( Menadione Sodium Bisulfate )
Cas No: 58-27-5
No Data 1 Metric Ton 100 Metric Ton/Month EAST CHEMSOURCES LIMITED Contact Supplier
Manufacturer Supply High Purity CAS 58-27-5 Menadione Vitamin K3 Vk3
Cas No: 58-27-5
USD $ 70.0-100.0 / Kilogram 1 Kilogram 5000 Kilogram/Month Xi'an Julong Bio-Tech Co., Ltd. Contact Supplier

58-27-5 Usage

Uses

The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.

Chemical properties

It appears as white crystalline or crystalline powder, being almost odorless and hygroscopic. Its color will change in case of light. It is easily soluble in water, slightly soluble in ethanol, but insoluble in ether and benzene.

Application

Biochemical research; clinical drugs belong to fat-soluble vitamins; it is clinically used as a hemostatic drug.
Vitamin K3 is mainly used as poultry feed enhancer at a dosage of 1-5mg/kg.
The goods can have addition reaction with sodium bisulfite to generate vitamin K3.
VK3. Used as raw material of feed additives; it can mainly promote the liver synthesis of prothrombin in livestock and poultry, and promote the liver synthesis of plasma coagulation factors as a hemostatic agent.
Traits: bright yellow crystal with very spicy smell. It is stable in the air and will be decomposed in sunlight. 1G can be dissolved in about 60ml ethanol, 10ml benzene and 50 ml vegetable oil. It is soluble in chloroform and carbon tetrachloride but insoluble in water. The ethanol solution was neutral to litmus paper. The solution will not be decomposed even when heated to 120 °C. It will be destroyed upon treatment with alkali and reducing agent. It is toxic with the half lethal dose (mouse, oral) being about 500 mG/kG. It is irritating. Its commodities still include sodium bisulfite manaquinone, appearing as white crystalline powder. It has no smell or with slightly special smell. It has hygroscopicity. It undergoes decomposition in case of light to turn into yellow or purple color. It is easily soluble in water, slightly soluble in ethanol, but almost insoluble in ether and benzene. Application: biochemical research

Production

There are two production processes. 1. Methyl naphthalene is obtained from the oxidization of chromic anhydride. 2-methyl naphthalene is dissolved in glacial acetic acid, stirred and cooled to temperature below 40 ℃. Slowly add the mixture of chromic anhydride and the same amount of water so that the temperature can be maintained at 35-40 ℃. After the completion of the addition, maintain the temperature at 40 ℃ for 0.5 h, the temperature was then raised to 70 ℃ for 45min, and further heated to 85 ℃ for 15min. Pour the reactants into a lot of water and stir continuously to precipitate out the 2-naphthoquinone. Filter and rinse the filter cake repeatedly with water, until the aqueous solution has no sour. Filter to get the 2-menenoquinone with a yield of 51%. 2-methyl naphthalene can also be made from sodium dichromate and potassium dichromate with the oxidation yield being roughly the same. 2. Cyclohexanone has cyclization reaction with butadiene to get 2-methyl naphthalene hydroquinone, followed by oxidation with chromic acid to obtain the final product. Dissolve the toluquinone in glacial acetic acid; send the butadiene to the required amount at temperature below 20 ℃; stand for 20 hours; heat to release the remaining butadiene and continue to heat to about 110 °C for refluxing of 3 hours. Then recycle 30% of glacial acetic acid through vacuum distillation and cooled to temperature below 40 ℃; slowly add the mixture of chromic acid and the same amount of water so that the temperature is maintained at 65-70 ℃. After the completion of the addition, maintain the temperature at 70-80 degree for 1h to obtain the menadione.
O-methyl naphthoquinone is used as raw material. It undergoes oxidation with glacial acetic acid and chromic anhydride, followed by addition with sodium bisulfite in ethanol to derive it.

Uses

Precursor to verious types of Vitamin K. Used as a micronutrient for livestock and pet foods.

Chemical Properties

Bright yellow crystals

Uses

antibacterial

Definition

ChEBI: A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group.

Uses

prothrombogenic agent

Purification Methods

Recrystallise it from 95% EtOH, or MeOH after filtration. It forms bright yellow crystals which are decomposed by light. Its solubility in EtOH is 1.7% and in *C6H6 it is 10%. It IRRITATES mucous membranes and skin. [Fieser J Biol Chem 133 391 1940, Beilstein 7 IV 2430.]

Brand name

Kappaxin (Sterling Winthrop); Kayquinone.
InChI:InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

58-27-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (M9429)  Menadione  meets USP testing specifications 58-27-5 M9429-100G 1,251.90CNY Detail
Sigma (M9429)  Menadione  meets USP testing specifications 58-27-5 M9429-25G 405.99CNY Detail
Sigma (M5625)  Menadione  crystalline 58-27-5 M5625-100G 1,102.14CNY Detail
Sigma (M5625)  Menadione  crystalline 58-27-5 M5625-25G 325.26CNY Detail
Supelco (47775)  Menadione(K3)  analytical standard 58-27-5 000000000000047775 286.65CNY Detail
USP (1381006)  Menadione  United States Pharmacopeia (USP) Reference Standard 58-27-5 1381006-200MG 4,662.45CNY Detail
Sigma-Aldrich (M0300000)  Menadione  European Pharmacopoeia (EP) Reference Standard 58-27-5 M0300000 1,880.19CNY Detail
Sigma-Aldrich (PHR1411)  Menadione  pharmaceutical secondary standard; traceable to USP, PhEur 58-27-5 PHR1411-500MG 718.73CNY Detail
Alfa Aesar (A13593)  2-Methyl-1,4-naphthoquinone, 98%    58-27-5 250g 3542.0CNY Detail
Alfa Aesar (A13593)  2-Methyl-1,4-naphthoquinone, 98%    58-27-5 50g 856.0CNY Detail
Alfa Aesar (A13593)  2-Methyl-1,4-naphthoquinone, 98%    58-27-5 10g 245.0CNY Detail
TCI America (M0373)  2-Methyl-1,4-naphthoquinone  >98.0%(HPLC)(T) 58-27-5 250g 1,970.00CNY Detail

58-27-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name menadione

1.2 Other means of identification

Product number -
Other names Aquakay

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-27-5 SDS

58-27-5Synthetic route

2-methyl-1,4-naphthohydroquinone
481-85-6

2-methyl-1,4-naphthohydroquinone

menadione
58-27-5

menadione

Conditions
ConditionsYield
With iodate form of Amberlyst A26 In dichloromethane at 20℃; for 2h; further reagent;100%
With sulfuric acid; sodium bromide In dichloromethane; water at 15℃; for 2.98h; Electrolysis;99%
With carbon dioxide; oxygen In water at 35 - 60℃; under 57005.7 - 62256.2 Torr; for 0.0833333h; Autoclave;96%
2-methylnaphthalen-1-ol
7469-77-4

2-methylnaphthalen-1-ol

menadione
58-27-5

menadione

Conditions
ConditionsYield
With Co(salN-Medpt); oxygen In acetonitrile for 0.5h;100%
Stage #1: 2-methylnaphthalen-1-ol In acetonitrile at 74.84℃;
Stage #2: With dihydrogen peroxide In acetonitrile for 0.75h; Reflux; chemoselective reaction;
97.3%
With sulfuric acid; dihydrogen peroxide In water at 36 - 40℃; for 6h; Temperature; Solvent; Green chemistry;94.7%
2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

menadione
58-27-5

menadione

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water at 75℃; for 5h; Product distribution / selectivity;100%
With C69H63Cl6N3O9(3-)*1.5Cu(2+); acetic acid In water at 40 - 100℃; for 14h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration;93%
With dihydrogen peroxide; acetic acid In acetonitrile Catalytic behavior; Solvent; Reflux;93%
2-methyl-5,6,9,10-tetrahydro-1,4-naphthoquinone

2-methyl-5,6,9,10-tetrahydro-1,4-naphthoquinone

menadione
58-27-5

menadione

Conditions
ConditionsYield
With palladium 10% on activated carbon In acetone for 24h; Reflux; Inert atmosphere;100%
With sodium dichromate; sulfuric acid; acetic acid a) 80-90 deg C, 1 h, b) RT, 12 h;93%
With manganese(II) bromide; copper(I) bromide In dimethyl sulfoxide at 85℃; under 600.06 Torr; for 26h; Temperature;91.3%
C11H10O2
92071-59-5

C11H10O2

menadione
58-27-5

menadione

Conditions
ConditionsYield
With palladium 10% on activated carbon In acetone Reflux;100%
Hykinone
130-37-0

Hykinone

menadione
58-27-5

menadione

Conditions
ConditionsYield
With sodium hydroxide In chloroform; water at 20℃; Product distribution / selectivity;100%
With water; sodium carbonate at 25℃; for 120h; Time;
2-methyl-5,8-dihydro-1,4-naphthalenediol
3090-46-8

2-methyl-5,8-dihydro-1,4-naphthalenediol

menadione
58-27-5

menadione

Conditions
ConditionsYield
With carbon dioxide; oxygen In water at 37 - 80℃; under 60756.1 - 69757 Torr; for 0.125h; Pressure; Temperature; Autoclave;98.4%
With lithium perchlorate In acetonitrile; tert-butyl alcohol at 16 - 18℃; for 8.6h; electrolysis on Pt electrodes;94%
With chromium(VI) oxide; acetic acid at 20℃;
2-methyl-5,6,7,8-tetrahydronaphthalene-1,4-diol
16368-80-2

2-methyl-5,6,7,8-tetrahydronaphthalene-1,4-diol

menadione
58-27-5

menadione

Conditions
ConditionsYield
With carbon dioxide; oxygen In water at 37 - 80℃; under 58505.9 - 72007.2 Torr; for 0.111111h; Autoclave;95.7%
1,4-dimethoxy-2-methylnaphthalene
53772-19-3

1,4-dimethoxy-2-methylnaphthalene

menadione
58-27-5

menadione

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 0.166667h; Oxidation; Demethylation;94%
With bis-[(trifluoroacetoxy)iodo]benzene In methanol; water at 20℃; for 0.5h;92%
With tert.-butylhydroperoxide; poly(bis-1,2-phenylene) diselenide In tert-butyl alcohol at 80℃; for 12h;90%
With ammonium persulfate; silver nitrate In water; acetonitrile for 18h; Ambient temperature;56%
phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

tert-butyl 3-cyanobutanoate

tert-butyl 3-cyanobutanoate

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: phthalic acid dimethyl ester; tert-butyl 3-cyanobutanoate With potassium tert-butylate In toluene at 100 - 105℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In water; toluene at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In water; toluene at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
92.3%
di-tert-butyliminoxyl
33802-06-1

di-tert-butyliminoxyl

2-methyl-1,4-napthohydroquinone

2-methyl-1,4-napthohydroquinone

menadione
58-27-5

menadione

Conditions
ConditionsYield
92%
phthalic acid di(tert-butyl)ester
30448-43-2

phthalic acid di(tert-butyl)ester

tert-butyl 3-cyanobutanoate

tert-butyl 3-cyanobutanoate

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: phthalic acid di(tert-butyl)ester; tert-butyl 3-cyanobutanoate With potassium tert-butylate In toluene at 100 - 105℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In water; toluene at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In water; toluene at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
91.9%
phthalic acid di(tert-butyl)ester
30448-43-2

phthalic acid di(tert-butyl)ester

C8H13NO2

C8H13NO2

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: phthalic acid di(tert-butyl)ester; C8H13NO2 With potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 100 - 105℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In 5,5-dimethyl-1,3-cyclohexadiene; water at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
91.9%
phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

methyl 3-cyanobutanoate

methyl 3-cyanobutanoate

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: phthalic acid dimethyl ester; methyl 3-cyanobutanoate With sodium methylate In methanol; toluene at 90 - 100℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In water; toluene at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In water; toluene at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
90.7%
2-methyl-5,8-dihydro-1,4-naphthoquinone
82654-73-7

2-methyl-5,8-dihydro-1,4-naphthoquinone

menadione
58-27-5

menadione

Conditions
ConditionsYield
With lithium perchlorate In acetonitrile at 16 - 17℃; for 3.2h; electrolysis on Pt electrodes;90%
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

menadione
58-27-5

menadione

Conditions
ConditionsYield
In tert-butyl alcohol for 12h; Methylation; UV-irradiation;90%
rac-ethyl 3-cyanobutanoate
22584-00-5

rac-ethyl 3-cyanobutanoate

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: rac-ethyl 3-cyanobutanoate; phthalic acid dimethyl ester With sodium ethanolate In methanol; toluene at 90 - 100℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In water; toluene at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In water; toluene at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
89%
phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

C8H13NO2

C8H13NO2

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: phthalic acid dimethyl ester; C8H13NO2 With sodium methylate In methanol; chlorobenzene at 90 - 100℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In water; chlorobenzene at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In water; chlorobenzene at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
88.3%
2-methylnaphthalen-1-ol
7469-77-4

2-methylnaphthalen-1-ol

lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

A

menadione
58-27-5

menadione

B

2-acetoxy-2-methylnaphthalen-1(2H)-one
76274-21-0

2-acetoxy-2-methylnaphthalen-1(2H)-one

Conditions
ConditionsYield
In benzene Ambient temperature;A 3%
B 88%
Diethyl phthalate
84-66-2

Diethyl phthalate

methyl 3-cyanobutanoate

methyl 3-cyanobutanoate

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: Diethyl phthalate; methyl 3-cyanobutanoate With sodium ethanolate In methanol; toluene at 90 - 100℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In water; toluene at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In water; toluene at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
87.8%
1-acetoxy-1,3-butadiene
1515-76-0

1-acetoxy-1,3-butadiene

2-methylbenzene-1,4-diol
95-71-6

2-methylbenzene-1,4-diol

menadione
58-27-5

menadione

Conditions
ConditionsYield
With oxygen In dimethyl sulfoxide at 55℃; for 24h; pH=4.5; Reagent/catalyst; Enzymatic reaction;85.8%
3-methylene-1,2,3,4-tetrahydronaphthalen-1-ol

3-methylene-1,2,3,4-tetrahydronaphthalen-1-ol

menadione
58-27-5

menadione

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 20℃; for 5h;81%
2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

A

6-methyl-1,4-naphthoquinone
605-93-6

6-methyl-1,4-naphthoquinone

B

menadione
58-27-5

menadione

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; acetic anhydride; acetic acid at 60℃; for 6.33333h; Product distribution / selectivity;A n/a
B 80%
With perchloric acid; dihydrogen peroxide; acetic anhydride; acetic acid at 60℃; for 6.33333h; Product distribution / selectivity;A n/a
B 80%
With phosphoric acid; dihydrogen peroxide; acetic anhydride; acetic acid at 60℃; for 6.33333h; Product distribution / selectivity;A n/a
B 75%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

A

menadione
58-27-5

menadione

B

2,3-dimethyl-5-hydroxy-1,4-naphthoquinone
80596-51-6

2,3-dimethyl-5-hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With copper(II) sulfate at 50℃; for 2h;A 60%
B 80%
1-acetoxybuta-1,3-diene
1515-76-0, 35694-19-0, 35694-20-3

1-acetoxybuta-1,3-diene

2-methylbenzene-1,4-diol
95-71-6

2-methylbenzene-1,4-diol

menadione
58-27-5

menadione

Conditions
ConditionsYield
With laccase In acetate buffer at 55℃; for 24h; pH=4.5; Diels-Alder reaction;75%
2-methylnaphthalen-1-ol
7469-77-4

2-methylnaphthalen-1-ol

A

menadione
58-27-5

menadione

B

2-acetoxy-2-methylnaphthalen-1(2H)-one
76274-21-0

2-acetoxy-2-methylnaphthalen-1(2H)-one

Conditions
ConditionsYield
With lead(IV) acetate In acetonitrile Ambient temperature;A 16%
B 74%
2-methylnaphthalen-1-ol
7469-77-4

2-methylnaphthalen-1-ol

A

phthiocol
483-55-6

phthiocol

B

menadione
58-27-5

menadione

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetic acid at 20℃; for 2h;A 6%
B 74%
3-methylnaphthalen-1-ol
13615-40-2

3-methylnaphthalen-1-ol

menadione
58-27-5

menadione

Conditions
ConditionsYield
With salcomine; oxygen In N,N-dimethyl-formamide for 3h; Ambient temperature;70%
With salcomine; oxygen In N,N-dimethyl-formamide for 3h;64%
(1S*,2S*)-2-methyl-1,2-dihydronaphthalen-1-ol

(1S*,2S*)-2-methyl-1,2-dihydronaphthalen-1-ol

A

menadione
58-27-5

menadione

B

3,3′-dimethyl-1,1′-binaphthalenyl-4,4′-diol
107866-11-5

3,3′-dimethyl-1,1′-binaphthalenyl-4,4′-diol

Conditions
ConditionsYield
With Jones reagent (excess) In acetone at 0℃;A n/a
B 68%
3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile
27613-27-0

3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

menadione
58-27-5

menadione

Conditions
ConditionsYield
Stage #1: 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile With lithium tert-butoxide In tetrahydrofuran at -78 - -60℃; for 0.416667h; Inert atmosphere;
Stage #2: methacrylic acid methyl ester In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
64%
menadione
58-27-5

menadione

2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone
15448-59-6, 61840-91-3, 82864-14-0, 105016-62-4

2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone

Conditions
ConditionsYield
With dihydrogen peroxide; β‐cyclodextrin In water at 25℃; for 96h; pH 9; other reagents (t-BuOOH, NaOCl, PhC(CH3)2OOH), MCPBA), other solvents (DMF, DMSO), addition of base (NaOH, NaHCO3, Na2CO3);100%
With dihydrogen peroxide; β‐cyclodextrin; alpha cyclodextrin In water at 25℃; for 96h; Product distribution; pH 9; other oxidizing agents (t-BuOOH, NaOCl, PhC(CH3)2OOH), MCPBA); other solvents (DMF, DMSO), addition of base (NaOH, Na2CO3, NaHCO3); enantioselectivity (up to 40percent ee by NMR); same reaction with further naphthoquinones;100%
With lithium hydroxide; tetrabutylammomium bromide; dihydrogen peroxide In toluene at 15 - 25℃; for 0.416667h; Epoxidation; ultrasonic irradiation;100%
menadione
58-27-5

menadione

2-methyl-1,4-naphthohydroquinone
481-85-6

2-methyl-1,4-naphthohydroquinone

Conditions
ConditionsYield
With sodium dithionite In diethyl ether; water100%
With sodium dithionite In diethyl ether; water at 20℃;100%
With sodium dithionite In diethyl ether; water100%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

menadione
58-27-5

menadione

Acetic acid (1S,2aR,8aR)-1,8a-dimethyl-3,8-dioxo-1,2,2a,3,8,8a-hexahydro-cyclobuta[b]naphthalen-1-yl ester
75858-24-1

Acetic acid (1S,2aR,8aR)-1,8a-dimethyl-3,8-dioxo-1,2,2a,3,8,8a-hexahydro-cyclobuta[b]naphthalen-1-yl ester

Conditions
ConditionsYield
In benzene for 1h; Irradiation;100%
menadione
58-27-5

menadione

prenylindium sesquiiodide

prenylindium sesquiiodide

2,3-dihydro-2-methyl-2-(3-methyl-but-2-enyl)-1,4-naphthoquinone
74785-15-2

2,3-dihydro-2-methyl-2-(3-methyl-but-2-enyl)-1,4-naphthoquinone

Conditions
ConditionsYield
In N,N-dimethyl-formamide at -23℃; for 3h;100%
Ge[N(C(CH3)3)(Si(CH3)3)]2

Ge[N(C(CH3)3)(Si(CH3)3)]2

menadione
58-27-5

menadione

Ge(N(Si(CH3)3)C(CH3)3)2OC6H(CH3)(CH(CH)2CH)O

Ge(N(Si(CH3)3)C(CH3)3)2OC6H(CH3)(CH(CH)2CH)O

Conditions
ConditionsYield
In tetrahydrofuran (Ar); stirring (1 h, -78°C); soln. filtn. off, drying (vac.); elem. anal.;100%
1-hexene
592-41-6

1-hexene

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

menadione
58-27-5

menadione

2-(1-butyl-3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-3-methyl-[1,4]naphthoquinone

2-(1-butyl-3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-3-methyl-[1,4]naphthoquinone

Conditions
ConditionsYield
With dibenzoyl peroxide In acetic acid for 4h; Heating;99%
1-(4-bromo-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid hydrazide

1-(4-bromo-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid hydrazide

menadione
58-27-5

menadione

N'-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(4-bromophenyl)-5-oxopyrrolidine-3-carbohydrazide
1342800-33-2

N'-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(4-bromophenyl)-5-oxopyrrolidine-3-carbohydrazide

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol for 19h; Reflux;99%
menadione
58-27-5

menadione

2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

2,3,4a-trimethyl-1,4,4a,9a-tetrahydro-anthraquinone

2,3,4a-trimethyl-1,4,4a,9a-tetrahydro-anthraquinone

Conditions
ConditionsYield
With tetradecafluorohexane; lithium perfluorooctane sulfonate In water at 25℃; for 72h; Diels-Alder reaction;98%
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

menadione
58-27-5

menadione

2-methyl-3-nonafluorobutyl-[1,4]naphthoquinone

2-methyl-3-nonafluorobutyl-[1,4]naphthoquinone

Conditions
ConditionsYield
With dibenzoyl peroxide In acetic acid for 4h; Heating;98%
menadione
58-27-5

menadione

(2S,3R)-2,3-epoxy-2-methyl-1,4-naphthoquinone

(2S,3R)-2,3-epoxy-2-methyl-1,4-naphthoquinone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C49H63Cl6N7O2*ClH; potassium hydroxide In tert-butyl methyl ether; water at 0℃; for 0.5h; enantioselective reaction;98%
With sodium hypochlorite; diphenylether; Cinchona alkaloid phase-transfer catalyst In chlorobenzene at -10℃;
C12H15N3O2
956593-14-9

C12H15N3O2

menadione
58-27-5

menadione

N'-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(3-methylphenyl)-5-oxopyrrolidine-3-carbohydrazide
1342800-28-5

N'-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(3-methylphenyl)-5-oxopyrrolidine-3-carbohydrazide

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol for 19h; Reflux;98%
menadione
58-27-5

menadione

1,3-dihydro-imidazole-2-thione
872-35-5

1,3-dihydro-imidazole-2-thione

2-(1H-imidazole-2-ylthio)-3-methylnaphthalene-1,4-dione
1449761-93-6

2-(1H-imidazole-2-ylthio)-3-methylnaphthalene-1,4-dione

Conditions
ConditionsYield
In methanol at 20℃; for 8h;98%
menadione
58-27-5

menadione

2-(5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-ylidene)acetaldehyde

2-(5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-ylidene)acetaldehyde

C25H22O2

C25H22O2

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 20℃; for 20h;98%
menadione
58-27-5

menadione

dimethyl sulfate
77-78-1

dimethyl sulfate

1,4-dimethoxy-2-methylnaphthalene
53772-19-3

1,4-dimethoxy-2-methylnaphthalene

Conditions
ConditionsYield
Stage #1: menadione With palladium on activated charcoal; hydrogen In methanol for 6h;
Stage #2: dimethyl sulfate With sodium methylate In methanol at 50℃; for 0.333333h; Inert atmosphere;
97.1%
Stage #1: menadione With hydrogenchloride; tin(ll) chloride In ethanol at 20℃; for 0.5h;
Stage #2: dimethyl sulfate With potassium hydroxide In ethanol; acetone at 60℃; for 2h;
73%
Stage #1: menadione With hydrogenchloride; tin(ll) chloride In ethanol at 20℃;
Stage #2: dimethyl sulfate With potassium hydroxide In acetone at 60℃;
Stage #1: menadione With hydrogenchloride; tin(ll) chloride In ethanol at 40℃; for 0.166667h;
Stage #2: dimethyl sulfate With potassium hydroxide In acetone at 20℃; for 2.5h; Further stages.;
Stage #1: menadione With sodium dithionite In ethyl acetate at 20℃; for 0.5h;
Stage #2: dimethyl sulfate With sodium methylate In isopropyl alcohol at 63℃; for 0.5h;
menadione
58-27-5

menadione

(5aS,5bR,11aS,11bR)-5a,11a-Dimethyl-5a,5b,11a,11b-tetrahydro-dibenzo[b,h]biphenylene-5,6,11,12-tetraone

(5aS,5bR,11aS,11bR)-5a,11a-Dimethyl-5a,5b,11a,11b-tetrahydro-dibenzo[b,h]biphenylene-5,6,11,12-tetraone

Conditions
ConditionsYield
2,4,6-tri(4-pyridyl)-1,3,5-triazine In water-d2 at 20℃; for 3h; Irradiation;96%
1-(4-chlorophenyl)-5-oxopyrrolidin-3-carbohydrazide

1-(4-chlorophenyl)-5-oxopyrrolidin-3-carbohydrazide

menadione
58-27-5

menadione

N'-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(4-chlorophenyl)-5-oxopyrrolidine-3-carbohydrazide
1342800-34-3

N'-(3-methyl-4-oxo-1,4-dihydronaphthalen-1-ylidene)-1-(4-chlorophenyl)-5-oxopyrrolidine-3-carbohydrazide

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol for 19h; Reflux;96%
menadione
58-27-5

menadione

cyclobutanone oxime ester

cyclobutanone oxime ester

4-(3-methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-phenyl-butyronitrile

4-(3-methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-phenyl-butyronitrile

Conditions
ConditionsYield
With (1,2-dimethoxyethane)dichloronickel(II); bathophenanthroline In acetonitrile at 100℃; for 6h; Sealed tube; Inert atmosphere;96%
menadione
58-27-5

menadione

2-bromo-3-methyl-[1,4]naphthoquinone
3129-39-3

2-bromo-3-methyl-[1,4]naphthoquinone

Conditions
ConditionsYield
With aluminum oxide; bromine for 2h; Ambient temperature; other reagents: iodine monobromide, acetic acid;95%
With N-chloro-succinimide; copper(II) chloride monohydrate In acetonitrile at 82℃; for 4h; regioselective reaction;95.9%
Stage #1: menadione With bromine In dichloromethane at 25℃; for 1h;
Stage #2: With pyridine In dichloromethane at 25℃; for 12h;
93%
formaldehyd
50-00-0

formaldehyd

menadione
58-27-5

menadione

2-(chloromethyl)-3-methylnaphthalene-1,4-dione
31599-79-8

2-(chloromethyl)-3-methylnaphthalene-1,4-dione

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 20℃;95%
With hydrogenchloride; acetic acid87%
With hydrogenchloride In water; acetic acid at 60 - 65℃; for 0.5h;86%

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